Electrochemical [3+3] Annulation of Phenol and Hydrazone: Synthesis of 1,3,4-Oxadiazines
The Journal of Organic Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Фев. 19, 2025
A
novel
[3+3]
cyclization
reaction
between
phenol
and
hydrazone
was
successfully
developed
under
electrochemically
driven
conditions.
This
provided
access
to
a
diverse
array
of
1,3,4-oxadiazinane
compounds
in
consistently
high
yields,
reaching
up
87%.
Notably,
the
exhibited
remarkable
tolerance
toward
broad
spectrum
both
substrates,
underscoring
its
versatility.
Moreover,
protocol
distinguished
itself
by
exceptional
atom
step
economy,
facilitating
efficient
construction
functionalized
1,3,4-oxadiazines.
The
synthetic
utility
this
approach
further
exemplified
scalability,
as
demonstrated
gram-scale
reactions,
substrate
scope.
Язык: Английский
Synthesis of Non-C2-Symmetric Biaryldiols via Organo-Electro Catalyzed Aryl–Aryl Dehydrogenative Cross-Coupling
Journal of the American Chemical Society,
Год журнала:
2025,
Номер
147(9), С. 7524 - 7532
Опубликована: Фев. 19, 2025
Despite
a
few
successful
examples,
controlling
the
enantioselectivity
in
asymmetric
synthesis
of
non-C2-symmetric
biaryldiols
has
long
been
challenging.
To
address
issues
and
regioselectivity,
we
introduced
novel
organoelectrocatalytic
strategy
enabling
aryl-aryl
dehydrogenative
cross-coupling
reactions.
Using
this
approach,
valuable
were
obtained
up
to
95%
yields
97%
enantiomeric
excesses
(ees),
these
compounds
could
be
further
applied
as
versatile
ligands
Detailed
mechanistic
studies
supported
sequential
diradical
followed
by
central-to-axial
chirality
conversion
pathway.
Язык: Английский